Sodium Hydroxide → 1773508-58-9

HRID 920785Notes

Reaction equation

HRID 920785 reaction equation
[F:1][CH:2]([F:15])[C:3]1([C:9]([O:11]C(C)C)=[O:10])[CH2:6][C:5]([F:8])([F:7])[CH2:4]1.[OH-].[Na+]>C(O)C.O>[F:15][CH:2]([F:1])[C:3]1([C:9]([OH:11])=[O:10])[CH2:6][C:5]([F:7])([F:8])[CH2:4]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 118061692HCID 118061692, compound

Product 1

HCID 1180617751773508-58-9Yield 74%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of Intermediate 304D (500 mg, 2.191 mmol) in ethanol (10 mL) and water (2 mL) was added NaOH (2.191 mL, 10.96 mmol, 5 M in water) and the resulting solution was stirred at RT for 4 h. EtOH was removed under reduced pressure, and the aqueous solution was acidified with a 1.5 N aq. solution of HCl which was then extracted with DCM (3×30 mL). The combined organic layer was washed with brine, dried over Na2SO4, filtered and the filtrate was concentrated to afford Intermediate 304E as a pale yellow liquid (300 mg, 74% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 13.87 (br. s., 1H), 6.21-6.63 (m, 1H), 2.77-3.11 (m, 4H).

Workup

  1. customEtOH was removed under reduced pressure
  2. extractionwas then extracted with DCM (3×30 mL)
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-f84b6ec0d25c48ceb826828faac39b9f
Source dataset
uspto-grants-2016_03
Patent number
US09273058B2

Reaction notes

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